Biological synthesis of <scp>l</scp>-ascorbic acid in animal tissues: conversion of <scp>d</scp>-glucuronolactone and <scp>l</scp>-gulonolactone into <scp>l</scp>-ascorbic acid

Chatterjee, Indu B.; Chatterjee, Gaurav; Ghosh, Nilabja; Ghosh, J. J.; Guha, B. C.

doi:10.1042/bj0760279

Cited by 49 publications

(19 citation statements)

References 21 publications

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“…4) but also in biochemical context. Glucuronolactone is a precursor of ascorbic acid in the metabolic pathway in animals (Chatterjee, Chatterjee, Ghosh, Ghosh & Guha, 1960) and is converted to ascorbic acid in the human body (Baker, Bierman & Plough, 1960).…”

Section: Discussionmentioning

confidence: 99%

Structure of the crystalline dimer of dehydro-L-ascorbic acid

Hvoslef¹

1972

Acta Crystallogr Sect B

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The first oxidation product of vitamin C is dehydro-L-ascorbic acid, Cx2HlzO12, which is dimeric in the crystalline state. The molecular and crystal structure has been determined by means of three-dimensional X-ray data and the parameters have been refined to a final R index of 5.6 % for the observed reflexions. The monoclinic unit cell (space group C2) contains two molecules and has the lattice parameters a= 15-728, b= 5"530, c=9.453 A and fl= 130.56 °. The molecule has twofold symmetry and comprises a system of five fused rings; non-planar 7-1actone and furanose rings are attached to a central dioxan ring in the 'twisted boat' conformation. The C-O distances within the rings vary between 1.338 and 1.448 A, while the C-C distances have a mean value of 1.524/~. The external, axially bonded C-OH groups have relatively short C-O distances and contain, in addition to the carbonyl groups, the only oxygen atoms taking part in hydrogen bonding. Each molecule is linked to eight others by one such bond to each of them.

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Section: Discussionmentioning

confidence: 99%

Structure of the crystalline dimer of dehydro-L-ascorbic acid

Hvoslef¹

1972

Acta Crystallogr Sect B

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“…Fishes like elasmobranchs, lampreys, sturgeons, and lungfishes express Gulo and synthesize ascorbic acid in the kidney (11). In general, Gulo/GULO is a microsomal enzyme that catalyzes the aerobic conversion of gulonolactone to ascorbate, with the production of hydrogen peroxide (12, 13). Invertebrates, teleost fishes, some passerine birds, guinea pigs, bats, and anthropoid primates, including humans, lack functional Gulo/GULO (14, 15) and therefore need a dietary intake of ascorbic acid as vitamin C. The inability of these animals to synthesize ascorbic acid is due to an inactivated gulo gene encoding for a nonfunctional enzyme (11, 16).…”

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confidence: 99%

L‐gulono‐7‐lactone oxidase expression and vitamin C synthesis in the brain and kidney of the African lungfish,Protopterus annectens

et al. 2014

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This study aimed to test the hypothesis that the brain of Protopterus annectens expressed L-gulono-γ-lactone oxidase (gulo/Gulo), the enzyme catalyzing the last step of ascorbate biosynthesis, and could maintain high concentrations of ascorbate during estivation. We cloned and sequenced gulo from the kidney of P. annectens and performed quantitative PCR to determine its mRNA expression in kidney and brain. Gulo activity was assayed and its protein abundance was determined by Western blot using custom-made anti-Gulo antibody. Effects of estivation on concentrations of ascorbate and dehydroascorbate in the kidney and brain were also determined. Both brain and kidney, but not liver, of P. annectens expressed gulo/Gulo. Desiccation induced P. annectens to estivate, and 6 mo of estivation led to drastic decreases in gulo/Gulo expression and ascorbate concentration in the kidney. However, high concentrations of ascorbate and ascorbate + dehydroascorbate were maintained in the brain during estivation, probably resulting from in situ ascorbate synthesis. Control fish were placed in freshwater, where they were fully active in a favorable environment unlike estivation on land. The ability to synthesize ascorbate to ameliorate oxidative stress directly in the brain might contribute to the ability of P. annectens to undergo prolonged estivation on land.

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“…It is converted into L-ascorbic acid in animals (Chatterjee, Chatterjee, Ghosh, Ghosh & Guha, 1960) and in the human body (Baker, Bierman & Plough, 1960), and has been shown to have an antihypnotic action against sodium 5,5-diethylbarbiturate (Tamura, Tsutsumi & Kizu, 1962). The molecule was originally believed to contain a sixmembered pyranose and a five-membered lactone ring as shown in (I), since it is derived from glucuronic acid, which has the pyranose structure (II) like the anion in potassium glucuronate (Gurr, 1963;Furberg, Hammer & Mostad, 1963).…”

Section: Introductionmentioning

confidence: 99%

The crystal structure of β-D-glucurono-γ-lactone

Kim¹,

Rosenstein²,

Corfield³

1967

Acta Cryst

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The crystal structure of fl-D-glucurono-~,-lactone, C6H806, has two molecules in a cell with a= 6.753, b = 7.488, c = 6"608/~, fl= 93" 18 °, space group P21. The structure was solved from the three-dimensional sharpened Patterson function using multiple minimum function and convolution methods on an IBM 1620 computer. Both photographic and automatic diffractometer data were measured. The former gave a terminal R index of 10 ~o and the latter 4 ~o. The molecule was found to have fused five-membered lactone and furanose rings, in agreement with an earlier deduction from chemical evidence. The rings, neither of which is planar, are inclined to each other so that the best planes containing four atoms in each make a dihedral angle of 111.3 °. The lactone group is not planar, having a carbon atom 0.26/~ O II out of the plane of the C-C-O group, which is planar. The C-O bond adjacent to the carbonyl group is 0"10/~ shorter than the other formal single C-O bonds in the molecule. The molecules are associated in the crystal by a very simple system of hydrogen bonding, which excludes one hydroxyl group and the ring oxygen atoms.

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Biological synthesis of l-ascorbic acid in animal tissues: conversion of d-glucuronolactone and l-gulonolactone into l-ascorbic acid

Cited by 49 publications

References 21 publications

Structure of the crystalline dimer of dehydro-L-ascorbic acid

Structure of the crystalline dimer of dehydro-L-ascorbic acid

L‐gulono‐7‐lactone oxidase expression and vitamin C synthesis in the brain and kidney of the African lungfish,Protopterus annectens

The crystal structure of β-D-glucurono-γ-lactone

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